HCID 23401710, compound → Benzenesulfonamide

HRID 1063969Notes

Reaction equation

HRID 1063969 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11](C2C=C(F)C=CC=2F)[C@H](C)CCCBr)(=[O:10])=[O:9])=[CH:4][CH:3]=1>CCOCC>[C:5]1([S:8]([NH2:11])(=[O:10])=[O:9])[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

3

Reactant 1

HCID 23401710HCID 23401710, compound

Product 1

HCID 7370BenzenesulfonamideYield 50%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 4-chloro-N-(2,5-difluorophenyl)-N-[(R)-1-methyl-4-bromobutyl]benzenesulfonamide (0.194 g, 0.427 mmol) in ether (4 mL) was added AgNO2 (0.395 g, 2.56 mmol) at 22° C. The resulting mixture was allowed to stir at 22° C. for 4 days. The mixture was filtered and concentrated under reduced pressure. Silica gel chromatography (1:9 ethyl acetate:hexanes) of the concentrate afforded 0.0913 g of 4-chloro-N-(2,5-difluorophenyl)-N-[(R)-1-methyl-4-nitrobutyl]]-benzenesulfonamide as a light brown oil in 50% yield. MS (ESI) 419.1 (M+H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-81b9537c2edd403688052a4280316f4b
Source dataset
uspto-grants-2005_11
Patent number
US06967196B1

Reaction notes

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